Stockbridge Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Stockbridge, Massachusetts, USA

Too Good AKA 2 Goodrich St
|
10.0 (2 Reviews)
8 Bedrooms 8 Guests
The Inn at Stockbridge
From£322 per night
|
9.8 (99 Reviews)
1 Bedroom 2 Guests
Stockbridge pied-à-terre
10.0 (15 Reviews)
1 Bedroom 3 Guests
The Inn at Stockbridge
From£373 per night
|
9.1 (8 Reviews)
13 Bedrooms 28 Guests
The Red Lion Inn
From£196 per night
|
8.8 (1005 Reviews)
1 Bedroom 2 Guests
Fabulous Tanglewood Getaway!
10.0 (14 Reviews)
1 Bedroom 4 Guests
Steps to Downtown Stockbridge: Home w/Patio!
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8.0 (1 Review)
2 Bedrooms 5 Guests
Tanglewood Suites
From£162 per night
6.4 (22 Reviews)
1 Bedroom 2 Guests
Hearth House | Prime Location!
10.0 (1 Review)
2 Bedrooms 5 Guests
2 Mi to Norman Rockwell Museum: Stockbridge Apt!
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8.0 (1 Review)
1 Bedroom 2 Guests
Light-filled Carpenter's Cottage w/EV charger!
9.8 (10 Reviews)
1 Bedroom 2 Guests
The Cottage
From£202 per night
|
5.4 (63 Reviews)
2 Bedrooms 6 Guests
Artist's Camp on Lake Mahkeenac
9.6 (21 Reviews)
2 Bedrooms 4 Guests
Stockbridge Retreat w/Pool & Hot Tub!
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New
4 Bedrooms 10 Guests
Cozy Stockbridge Cabin - Walk to Beach & Lake!
9.4 (15 Reviews)
2 Bedrooms 4 Guests
Beaver Creek by AvantStay
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New
4 Bedrooms 8 Guests
Stockbridge Village in Summer
9.2 (22 Reviews)
2 Bedrooms 4 Guests
The Red Lion Inn
From£166 per night
|
8.0 (300 Reviews)
108 Bedrooms 58 Guests
Stockbridge In-town Escape
New
2 Bedrooms 4 Guests
Just a min from Downtown Stockbridge on 11 Acres
10.0 (80 Reviews)
4 Bedrooms 8 Guests
Historic Stockbridge Villa on 25 acres
10.0 (18 Reviews)
11 Bedrooms 16 Guests
Brand New Barn House w/EV charger
10.0 (4 Reviews)
3 Bedrooms 6 Guests
General Williams Estate House Lenox/Stockbridge
9.8 (118 Reviews)
6 Bedrooms 12 Guests
A Grand property in Historic Stockbridge
9.8 (107 Reviews)
6 Bedrooms 12 Guests
Classic Berkshire Retreat
9.8 (12 Reviews)
3 Bedrooms 10 Guests
Summer in the Berkshires!
9.6 (5 Reviews)
3 Bedrooms 7 Guests
Stockbridge Retreat w/Pool & Hot Tub!
9.6 (4 Reviews)
4 Bedrooms 10 Guests
Light-filled Carpenter's Cottage
10.0 (1 Review)
1 Bedroom 2 Guests
CABIN FEVER IN STOCKBRIDGE
9.2 (14 Reviews)
2 Bedrooms 6 Guests
One block from Main St Stockbridge
New
2 Bedrooms 3 Guests
Stockbridge Home, Come Experience The Berkshires!
10.0 (33 Reviews)
3 Bedrooms 6 Guests
Stockbridge Estate with Mountain Views
10.0 (3 Reviews)
4 Bedrooms 8 Guests
Home with Pool on 10 Acres
New
3 Bedrooms 6 Guests
Light-filled Carpenter's Cottage in Stockbridge
10.0 (5 Reviews)
1 Bedroom 2 Guests
1780 Colonial Hilltop Manor - Amazing location
10.0 (3 Reviews)
4 Bedrooms 9 Guests
Stockbridge renovated classic- picture perfect
10.0 (3 Reviews)
4 Bedrooms 8 Guests
Rockspring by AvantStay | Huge Berkshires Estate
8.6 (11 Reviews)
6 Bedrooms 14 Guests
Historic Stockbridge, On Main Street, 3 Bedroom!
4.8 (6 Reviews)
3 Bedrooms 7 Guests
Historic Two Bedroom, Downtown Stockbridge
4.0 (4 Reviews)
2 Bedrooms 5 Guests
Holmes Suite PRIME Downtown Stockbridge
4.0 (1 Review)
1 Bedroom 3 Guests

About Stockbridge Vacation Rentals

With more than 70 Stockbridge vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Stockbridge.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Stockbridge, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Stockbridge. Places to stay near Stockbridge are 1584.31 ft² on average, with prices averaging £423 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Stockbridge with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Stockbridge?

What are the top vacation rentals in Stockbridge?

How many Rentbyowner vacation rentals are available in Stockbridge?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 70 in the Stockbridge area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Stockbridge.